1-(chloromethyl)-4-nitrobenzene

• ChemBase ID: 104422
• Molecular Formular: C7H6ClNO2
• Molecular Mass: 171.58104
• Monoisotopic Mass: 171.00870612
• SMILES: [O-][N+](=O)c1ccc(CCl)cc1
• Canonical SMILES: ClCc1ccc(cc1)[N+](=O)[O-]
• InChI: InChI=1S/C7H6ClNO2/c8-5-6-1-3-7(4-2-6)9(10)11/h1-4H,5H2
• InChIKey: KGCNHWXDPDPSBV-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 1-(chloromethyl)-4-nitrobenzene
• IUPAC Traditional name: 1-(chloromethyl)-4-nitrobenzene
• Synonyms: 4-Nitrobenzyl chloride; 1-(chloromethyl)-4-nitrobenzene; 4-Nitrobenzyl chloride; α-Chloro-4-nitrotoluene; p-NITROBENZYL CHLORIDE; α-Chloro-4-nitrotoluene; 4-Nitrobenzyl chloride; alpha-Chloro-4-nitrotoluene; α-氯-4-硝基甲苯; 4-硝基苄氯

Database IDs

• CAS Number: 100-14-1
• EC Number: 202-822-7
• MDL Number: MFCD00007374
• Beilstein Number: 387187
• PubChem SID: 162092765; 24886520; 24848454
• PubChem CID: 7482

CALCULATED PROPERTIES

• H Acceptors: 2
• H Donor: 0
• LogD (pH = 5.5): 2.500472
• LogD (pH = 7.4): 2.500472
• Log P: 2.500472
• Molar Refractivity: 42.2454 cm^3
• Polarizability: 15.909911 Å^3
• Polar Surface Area: 43.14 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 70-73 °C; 70-73 °C(lit.); 70-73°C; 70-74°C

Safety Information

• Storage Condition: 2-8°C
• RTECS: XS9093000
• European Hazard Symbols: Corrosive (C); X; Irritant (Xi); Harmful (Xn)
• UN Number: 3261; UN3261
• German water hazard class: 3
• Hazard Class: 8
• Packing Group: 2; II
• Australian Hazchem: 2X
• Risk Statements: 20/22-34-68; 22-34; R:22-30-36/37/38
• Safety Statements: 26-36/37/39-45; S:25-26-36/37/39
• EU Classification: C4
• EU Hazard Identification Number: 8B
• Emergency Response Guidebook(ERG) Number: 154
• TSCA Listed: 是
• GHS Pictograms: GHS05; GHS06; GHS07; GHS08
• GHS Signal Word: Danger
• GHS Hazard statements: H301-H332-H314-H318-H341; H302-H314
• GHS Precautionary statements: P260-P301+P310-P303+P361+P353-P305+P351+P338-P405-P501A; P280-P305 + P351 + P338-P310
• Personal Protective Equipment: Eyeshields, Faceshields, full-face particle respirator type N100 (US), Gloves, respirator cartridge type N100 (US), type P1 (EN143) respirator filter, type P3 (EN 143) respirator cartridges
• RID/ADR: UN 3261 8/PG 2

Product Information

• Purity: ≥99.0% (HPLC); 99%
• Grade: purum
• Impurities: ~1% 4-nitrobenzoic acid
• Linear Formula: O2NC6H4CH2Cl

DETAILS

MP Biomedicals - 02155865

(4-Nitrobenzyl chloride; α-Chloro-4-nitrotoluene)

Sigma Aldrich - 140112

Packaging
25, 100 g in glass bottle
Application
Used to prepare unsymmetrically N,N′-bis(substituted) 4,13-diaza-18-crown-6-ether derivatives.1

REFERENCES

• Reagent for carboxyl protection in peptide synthesis. Derivatives are stable to HBr, but cleaved by hydrogenolysis: J. Am. Chem. Soc., 81, 5691 (1959); J. Chem. Soc., 4922 (1965). See also 4-Nitrobenzyl alcohol, A15742, 4-Nitrobenzyl bromide, A15236, and Appendix 6.
• Has also been used for protection of the thiol group: J. Org. Chem., 37, 3550 (1972); J. Chem. Soc., Chem. Commun., 12 (1974).